| Title: | "Aphid-repellent, ladybug-attraction activities, and binding mechanism of methyl salicylate derivatives containing geraniol moiety" |
| Author(s): | Yang ZK; Qu C; Pan SX; Liu Y; Shi Z; Luo C; Qin YG; Yang XL; |
| Address: | "Innovation Center of Pesticide Research, Department of Applied Chemistry, College of Science, China Agricultural University, Beijing, P. R. China. Institute of Plant Protection, Beijing Academy of Agriculture and Forestry Sciences, Beijing, P. R. China. Department of Entomology and MOA Key Laboratory for Monitoring and Environment-Friendly Control of Crop Pests, College of Plant Protection, China Agricultural University, Beijing, China" |
| ISSN/ISBN: | 1526-4998 (Electronic) 1526-498X (Linking) |
| Abstract: | "BACKGROUND: Aphids have been mainly controlled by traditional chemical insecticides, resulting in unamiable risk to the environment over the last decades. Push-pull strategy is regarded as a promising eco-friendly approach for aphid management through repelling aphid away and attracting their natural enemy. Methyl salicylate (MeSA), one of typical HIPVs (herbivore-induced plant volatiles), can repel aphids and attract ladybugs. Our previous studies discovered a new lead compound 3e, a salicylate-substituted carboxyl (E)-beta-farnesene derivative that had effective aphid-repellent activity. However, whether 3e has attractive activity to ladybug like MeSA is unknown. Meanwhile, to discover a new derivative for both deterring aphid and recruiting ladybug is meaningful for green control of aphids. RESULTS: Through the structural optimization of 3e, 14 new derivatives were designed and synthesized. Among them, compounds 4e and 4i had good aphid (Acyrthosiphon pisum) repellent activity, and compounds 3e, 4e and 4i had significant ladybug (Harmonia axyridis) attractive activity to males. Particularly, 4i exhibited manifest attractive effect on the females as well. Binding mechanism showed that 4i not only bound effectively with the aphid (Acyrthosiphon pisum) target ApisOBP9 thanks to its multiple hydrophobic interactions and hydrogen-bond, but also had strong binding affinity with ladybug target HaxyOBP15 due to the suitable steric space. Additionally, 4i displayed low toxicity to bee Apis mellifera. CONCLUSION: Compound 3e does exhibit attractive activity to male ladybug as MeSA. However, the new derivative 4i, with both pleasant aphid-repellent and ladybug-attraction activities, can be considered as a novel potential push-pull candidate for aphid control in sustainable agriculture. (c) 2022 Society of Chemical Industry" |
| Keywords: | Animals Bees *Aphids/metabolism Salicylates/pharmacology/metabolism Acyclic Monoterpenes/pharmacology *Coleoptera *Insect Repellents/pharmacology HIPV derivatives aphids repellent ladybugs attraction methyl salicylate odorant-binding proteins push-pull st; |
| Notes: | "MedlineYang, Zhao-Kai Qu, Cheng Pan, Shi-Xiang Liu, Yan Shi, Zhuo Luo, Chen Qin, Yao-Guo Yang, Xin-Ling eng 2017YFD0200504/National Key Research and Development Plan/ 31801739/National Natural Science Foundation of China/ the National Key Research and Development Plan (No. 2017YFD0200504)/ the National Natural Science Foundation of China (No. 31801739)/ England 2022/10/20 Pest Manag Sci. 2023 Feb; 79(2):760-770. doi: 10.1002/ps.7245. Epub 2022 Nov 3" |
